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Synthesis and characterization of 1‐ and 2‐cinnamoyloxyacetonaphthones
Author(s) -
Venkatachalam T. K.,
Pierens G. K.,
Reutens D. C.
Publication year - 2010
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.2668
Subject(s) - chemistry , chemical shift , ring (chemistry) , nuclear magnetic resonance spectroscopy , characterization (materials science) , thiophene , proton nmr , proton , catalysis , cinnamic acid , high resolution , organic chemistry , nanotechnology , materials science , physics , remote sensing , quantum mechanics , geology
The synthesis of 1‐ and 2‐cinnamoyloxyacetonaphthones was achieved in one step using hydroxyl acetonaphthones and substituted cinnamic acids in the presence of a catalytic amount of phosphoroxychloride. Structural characterization was accomplished using high‐resolution nuclear magnetic resonance (NMR) spectroscopy. Chemical shifts of the compounds were compared and the change in the chemical shifts relative to electron‐donating and ‐withdrawing groups is presented. Introduction of a thiophene ring instead of phenyl‐substituted analogs caused shielding of the olefinic proton. Copyright © 2010 John Wiley & Sons, Ltd.